NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.16
Volume:	269.345
LogP:	2.772
LogD:	2.394
LogS:	-3.255
# Rotatable Bonds:	2
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.605
Synthetic Accessibility Score:	4.949
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.505
MDCK Permeability:	3.062333780690096e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.066
30% Bioavailability (F30%):	0.249

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.846
Plasma Protein Binding (PPB):	69.33948516845703%
Volume Distribution (VD):	1.216
Pgp-substrate:	34.528263092041016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.189
CYP1A2-substrate:	0.468
CYP2C19-inhibitor:	0.326
CYP2C19-substrate:	0.791
CYP2C9-inhibitor:	0.084
CYP2C9-substrate:	0.129
CYP2D6-inhibitor:	0.042
CYP2D6-substrate:	0.278
CYP3A4-inhibitor:	0.269
CYP3A4-substrate:	0.307

ADMET: Excretion

Clearance (CL):	9.878
Half-life (T1/2):	0.188

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.837
Drug-inuced Liver Injury (DILI):	0.269
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.952
Maximum Recommended Daily Dose:	0.235
Skin Sensitization:	0.642
Carcinogencity:	0.558
Eye Corrosion:	0.108
Eye Irritation:	0.08
Respiratory Toxicity:	0.969

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC78677

Natural Product ID:	NPC78677
*Common Name:**	Curcumanolide D
IUPAC Name:	(5R,6R,9S)-3-(2-hydroxypropan-2-yl)-6-methyl-9-prop-1-en-2-yl-1-oxaspiro[4.4]non-3-en-2-one
Synonyms:	Curcumanolide D
Standard InCHIKey:	PULYPMUFWFJDDV-ZETOZRRWSA-N
Standard InCHI:	InChI=1S/C15H22O3/c1-9(2)11-7-6-10(3)15(11)8-12(13(16)18-15)14(4,5)17/h8,10-11,17H,1,6-7H2,2-5H3/t10-,11+,15+/m1/s1
SMILES:	O=C1O[C@@]2(C=C1C(O)(C)C)[C@H](C)CC[C@H]2C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2332424
PubChem CID:	71578720
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO17780	Curcuma heyneana	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23387824]
NPO17780	Curcuma heyneana	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	<	65.0	%	PMID[564318]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC78677 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	1184
0.2-0.3	5924
0.3-0.4	15816
0.4-0.5	10555
0.5-0.6	6075
0.6-0.7	2627
0.7-0.8	336
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC59994
0.8333	Intermediate Similarity	NPC471185
0.8118	Intermediate Similarity	NPC146850
0.8118	Intermediate Similarity	NPC287015
0.8025	Intermediate Similarity	NPC53581
0.8025	Intermediate Similarity	NPC103987
0.8	Intermediate Similarity	NPC329852
0.7931	Intermediate Similarity	NPC45957
0.7931	Intermediate Similarity	NPC471657
0.7907	Intermediate Similarity	NPC245434
0.7857	Intermediate Similarity	NPC325031
0.7849	Intermediate Similarity	NPC64742
0.7826	Intermediate Similarity	NPC9812
0.7821	Intermediate Similarity	NPC265574
0.7791	Intermediate Similarity	NPC290052
0.7791	Intermediate Similarity	NPC156485
0.7778	Intermediate Similarity	NPC261607
0.7778	Intermediate Similarity	NPC300312
0.7778	Intermediate Similarity	NPC111114
0.7778	Intermediate Similarity	NPC2882
0.7727	Intermediate Similarity	NPC191283
0.7717	Intermediate Similarity	NPC469873
0.7692	Intermediate Similarity	NPC32862
0.7692	Intermediate Similarity	NPC40821
0.7692	Intermediate Similarity	NPC272293
0.7684	Intermediate Similarity	NPC206079
0.7667	Intermediate Similarity	NPC301969
0.7667	Intermediate Similarity	NPC37607
0.766	Intermediate Similarity	NPC244411
0.764	Intermediate Similarity	NPC260343
0.7619	Intermediate Similarity	NPC472013
0.7619	Intermediate Similarity	NPC476624
0.7609	Intermediate Similarity	NPC167219
0.759	Intermediate Similarity	NPC476439
0.7586	Intermediate Similarity	NPC154893
0.7586	Intermediate Similarity	NPC16887
0.7586	Intermediate Similarity	NPC37005
0.7586	Intermediate Similarity	NPC53011
0.7586	Intermediate Similarity	NPC474693
0.7579	Intermediate Similarity	NPC469864
0.7579	Intermediate Similarity	NPC469872
0.7561	Intermediate Similarity	NPC85831
0.7561	Intermediate Similarity	NPC215215
0.7561	Intermediate Similarity	NPC265921
0.7556	Intermediate Similarity	NPC212664
0.7553	Intermediate Similarity	NPC477949
0.7527	Intermediate Similarity	NPC52044
0.7527	Intermediate Similarity	NPC67584
0.75	Intermediate Similarity	NPC476627
0.75	Intermediate Similarity	NPC476628
0.75	Intermediate Similarity	NPC475860
0.75	Intermediate Similarity	NPC62670
0.75	Intermediate Similarity	NPC222210
0.75	Intermediate Similarity	NPC63445
0.75	Intermediate Similarity	NPC116139
0.75	Intermediate Similarity	NPC59646
0.75	Intermediate Similarity	NPC472954
0.75	Intermediate Similarity	NPC473659
0.75	Intermediate Similarity	NPC475099
0.75	Intermediate Similarity	NPC474694
0.75	Intermediate Similarity	NPC477950
0.75	Intermediate Similarity	NPC67183
0.7474	Intermediate Similarity	NPC221615
0.7473	Intermediate Similarity	NPC77337
0.7471	Intermediate Similarity	NPC245665
0.747	Intermediate Similarity	NPC476317
0.7449	Intermediate Similarity	NPC309190
0.7447	Intermediate Similarity	NPC213078
0.7444	Intermediate Similarity	NPC476805
0.7439	Intermediate Similarity	NPC474758
0.7423	Intermediate Similarity	NPC66110
0.7419	Intermediate Similarity	NPC262133
0.7419	Intermediate Similarity	NPC477131
0.7419	Intermediate Similarity	NPC470013
0.7419	Intermediate Similarity	NPC470521
0.7419	Intermediate Similarity	NPC323008
0.7419	Intermediate Similarity	NPC469632
0.7419	Intermediate Similarity	NPC470010
0.7416	Intermediate Similarity	NPC469483
0.7416	Intermediate Similarity	NPC261721
0.7416	Intermediate Similarity	NPC67493
0.7412	Intermediate Similarity	NPC469617
0.7407	Intermediate Similarity	NPC106309
0.7396	Intermediate Similarity	NPC280963
0.7391	Intermediate Similarity	NPC32494
0.7391	Intermediate Similarity	NPC472814
0.7391	Intermediate Similarity	NPC177037
0.7391	Intermediate Similarity	NPC472705
0.7391	Intermediate Similarity	NPC175842
0.7368	Intermediate Similarity	NPC108475
0.7368	Intermediate Similarity	NPC170143
0.7368	Intermediate Similarity	NPC161493
0.7368	Intermediate Similarity	NPC213947
0.7363	Intermediate Similarity	NPC225283
0.7356	Intermediate Similarity	NPC85772
0.7356	Intermediate Similarity	NPC20262
0.7356	Intermediate Similarity	NPC256750
0.734	Intermediate Similarity	NPC476488
0.734	Intermediate Similarity	NPC170120
0.734	Intermediate Similarity	NPC476487
0.734	Intermediate Similarity	NPC220221
0.7333	Intermediate Similarity	NPC72513
0.7333	Intermediate Similarity	NPC160138
0.7333	Intermediate Similarity	NPC201658
0.732	Intermediate Similarity	NPC150923
0.7312	Intermediate Similarity	NPC115021
0.7308	Intermediate Similarity	NPC470688
0.7303	Intermediate Similarity	NPC470755
0.7303	Intermediate Similarity	NPC125290
0.7303	Intermediate Similarity	NPC261380
0.7294	Intermediate Similarity	NPC299235
0.7294	Intermediate Similarity	NPC93763
0.7294	Intermediate Similarity	NPC267231
0.7294	Intermediate Similarity	NPC108816
0.7294	Intermediate Similarity	NPC470944
0.7284	Intermediate Similarity	NPC316029
0.7283	Intermediate Similarity	NPC106510
0.7283	Intermediate Similarity	NPC473448
0.7283	Intermediate Similarity	NPC3436
0.7283	Intermediate Similarity	NPC129419
0.7283	Intermediate Similarity	NPC71533
0.7273	Intermediate Similarity	NPC65350
0.7273	Intermediate Similarity	NPC472377
0.7273	Intermediate Similarity	NPC475947
0.7273	Intermediate Similarity	NPC472473
0.7262	Intermediate Similarity	NPC152017
0.7253	Intermediate Similarity	NPC471956
0.7253	Intermediate Similarity	NPC91248
0.7253	Intermediate Similarity	NPC476803
0.7241	Intermediate Similarity	NPC471325
0.7234	Intermediate Similarity	NPC127019
0.7234	Intermediate Similarity	NPC53685
0.7234	Intermediate Similarity	NPC198853
0.7234	Intermediate Similarity	NPC96541
0.7229	Intermediate Similarity	NPC7382
0.7222	Intermediate Similarity	NPC305475
0.7222	Intermediate Similarity	NPC475461
0.7209	Intermediate Similarity	NPC84185
0.7209	Intermediate Similarity	NPC178277
0.7209	Intermediate Similarity	NPC55304
0.7209	Intermediate Similarity	NPC471890
0.7209	Intermediate Similarity	NPC182550
0.7209	Intermediate Similarity	NPC226226
0.7209	Intermediate Similarity	NPC66677
0.7204	Intermediate Similarity	NPC131209
0.7204	Intermediate Similarity	NPC470520
0.7204	Intermediate Similarity	NPC158061
0.7204	Intermediate Similarity	NPC133698
0.7195	Intermediate Similarity	NPC29328
0.7191	Intermediate Similarity	NPC14575
0.7191	Intermediate Similarity	NPC476804
0.7191	Intermediate Similarity	NPC90446
0.7191	Intermediate Similarity	NPC158756
0.7191	Intermediate Similarity	NPC475100
0.7191	Intermediate Similarity	NPC196487
0.7191	Intermediate Similarity	NPC82297
0.7191	Intermediate Similarity	NPC114979
0.7191	Intermediate Similarity	NPC96259
0.7191	Intermediate Similarity	NPC191476
0.7191	Intermediate Similarity	NPC141193
0.7188	Intermediate Similarity	NPC471462
0.7176	Intermediate Similarity	NPC7563
0.7176	Intermediate Similarity	NPC472014
0.7176	Intermediate Similarity	NPC320630
0.7176	Intermediate Similarity	NPC116177
0.7174	Intermediate Similarity	NPC295312
0.7174	Intermediate Similarity	NPC205548
0.7174	Intermediate Similarity	NPC268298
0.716	Intermediate Similarity	NPC232812
0.7159	Intermediate Similarity	NPC26624
0.7158	Intermediate Similarity	NPC304886
0.7158	Intermediate Similarity	NPC213698
0.7143	Intermediate Similarity	NPC68624
0.7143	Intermediate Similarity	NPC77501
0.7143	Intermediate Similarity	NPC312561
0.7128	Intermediate Similarity	NPC469692
0.7128	Intermediate Similarity	NPC469645
0.7126	Intermediate Similarity	NPC47747
0.7126	Intermediate Similarity	NPC10636
0.7126	Intermediate Similarity	NPC276356
0.7125	Intermediate Similarity	NPC472266
0.7113	Intermediate Similarity	NPC471610
0.7113	Intermediate Similarity	NPC141191
0.7111	Intermediate Similarity	NPC300082
0.7111	Intermediate Similarity	NPC11804
0.7111	Intermediate Similarity	NPC165162
0.7111	Intermediate Similarity	NPC284534
0.7111	Intermediate Similarity	NPC204105
0.7111	Intermediate Similarity	NPC255307
0.71	Intermediate Similarity	NPC100487
0.7097	Intermediate Similarity	NPC471184
0.7097	Intermediate Similarity	NPC51486
0.7093	Intermediate Similarity	NPC196653
0.7093	Intermediate Similarity	NPC471465
0.7093	Intermediate Similarity	NPC128276
0.7093	Intermediate Similarity	NPC172066
0.7083	Intermediate Similarity	NPC98165
0.7083	Intermediate Similarity	NPC242848
0.7083	Intermediate Similarity	NPC230800
0.7079	Intermediate Similarity	NPC321385

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC78677 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1763
0.2-0.3	4134
0.3-0.4	2221
0.4-0.5	541
0.5-0.6	273
0.6-0.7	45
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7473	Intermediate Similarity	NPD5785	Approved
0.7303	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5363	Approved
0.7273	Intermediate Similarity	NPD5362	Discontinued
0.7126	Intermediate Similarity	NPD4820	Approved
0.7126	Intermediate Similarity	NPD4819	Approved
0.7126	Intermediate Similarity	NPD4821	Approved
0.7126	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4822	Approved
0.7079	Intermediate Similarity	NPD5331	Approved
0.7079	Intermediate Similarity	NPD5332	Approved
0.7045	Intermediate Similarity	NPD4790	Discontinued
0.6979	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4270	Approved
0.6966	Remote Similarity	NPD4269	Approved
0.6961	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4225	Approved
0.6897	Remote Similarity	NPD4268	Approved
0.6897	Remote Similarity	NPD4271	Approved
0.6854	Remote Similarity	NPD5369	Approved
0.6848	Remote Similarity	NPD5786	Approved
0.6848	Remote Similarity	NPD4249	Approved
0.6842	Remote Similarity	NPD7637	Suspended
0.6809	Remote Similarity	NPD1695	Approved
0.6778	Remote Similarity	NPD5209	Approved
0.6774	Remote Similarity	NPD4250	Approved
0.6774	Remote Similarity	NPD4251	Approved
0.6762	Remote Similarity	NPD6371	Approved
0.6742	Remote Similarity	NPD4252	Approved
0.6703	Remote Similarity	NPD7154	Phase 3
0.6667	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7115	Discovery
0.6517	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD5693	Phase 1
0.6481	Remote Similarity	NPD6053	Discontinued
0.6465	Remote Similarity	NPD5695	Phase 3
0.6452	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD6435	Approved
0.6392	Remote Similarity	NPD7838	Discovery
0.6392	Remote Similarity	NPD46	Approved
0.6392	Remote Similarity	NPD6698	Approved
0.6383	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7639	Approved
0.6373	Remote Similarity	NPD7640	Approved
0.6337	Remote Similarity	NPD6084	Phase 2
0.6337	Remote Similarity	NPD6083	Phase 2
0.6275	Remote Similarity	NPD7638	Approved
0.6275	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5696	Approved
0.6264	Remote Similarity	NPD4195	Approved
0.6263	Remote Similarity	NPD5778	Approved
0.6263	Remote Similarity	NPD5779	Approved
0.6237	Remote Similarity	NPD4223	Phase 3
0.6237	Remote Similarity	NPD4221	Approved
0.6224	Remote Similarity	NPD5207	Approved
0.6211	Remote Similarity	NPD1694	Approved
0.6196	Remote Similarity	NPD5368	Approved
0.6186	Remote Similarity	NPD5208	Approved
0.6162	Remote Similarity	NPD5281	Approved
0.6162	Remote Similarity	NPD7983	Approved
0.6162	Remote Similarity	NPD5284	Approved
0.6154	Remote Similarity	NPD5344	Discontinued
0.6146	Remote Similarity	NPD5690	Phase 2
0.6146	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD6051	Approved
0.6122	Remote Similarity	NPD6904	Approved
0.6122	Remote Similarity	NPD6080	Approved
0.6122	Remote Similarity	NPD6673	Approved
0.6122	Remote Similarity	NPD5370	Suspended
0.6105	Remote Similarity	NPD4197	Approved
0.6061	Remote Similarity	NPD5692	Phase 3
0.6058	Remote Similarity	NPD6648	Approved
0.6044	Remote Similarity	NPD4756	Discovery
0.6042	Remote Similarity	NPD5329	Approved
0.604	Remote Similarity	NPD6001	Approved
0.604	Remote Similarity	NPD5282	Discontinued
0.602	Remote Similarity	NPD6903	Approved
0.602	Remote Similarity	NPD4518	Approved
0.6019	Remote Similarity	NPD5697	Approved
0.6	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7331	Phase 2
0.6	Remote Similarity	NPD5694	Approved
0.6	Remote Similarity	NPD6050	Approved
0.6	Remote Similarity	NPD6695	Phase 3
0.598	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD7146	Approved
0.5979	Remote Similarity	NPD4688	Approved
0.5979	Remote Similarity	NPD4694	Approved
0.5979	Remote Similarity	NPD5330	Approved
0.5979	Remote Similarity	NPD6098	Approved
0.5979	Remote Similarity	NPD7334	Approved
0.5979	Remote Similarity	NPD4693	Phase 3
0.5979	Remote Similarity	NPD5205	Approved
0.5979	Remote Similarity	NPD7521	Approved
0.5979	Remote Similarity	NPD4690	Approved
0.5979	Remote Similarity	NPD5280	Approved
0.5979	Remote Similarity	NPD4138	Approved
0.5979	Remote Similarity	NPD6409	Approved
0.5979	Remote Similarity	NPD4689	Approved
0.5979	Remote Similarity	NPD6684	Approved
0.5963	Remote Similarity	NPD6686	Approved
0.5963	Remote Similarity	NPD6899	Approved
0.5963	Remote Similarity	NPD7320	Approved
0.5963	Remote Similarity	NPD6881	Approved
0.596	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.596	Remote Similarity	NPD4753	Phase 2
0.596	Remote Similarity	NPD6101	Approved
0.595	Remote Similarity	NPD7319	Approved
0.5941	Remote Similarity	NPD6399	Phase 3
0.5938	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6675	Approved
0.5926	Remote Similarity	NPD5739	Approved
0.5926	Remote Similarity	NPD7128	Approved
0.5926	Remote Similarity	NPD6402	Approved
0.5922	Remote Similarity	NPD7839	Suspended
0.5922	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD7328	Approved
0.5913	Remote Similarity	NPD7327	Approved
0.5909	Remote Similarity	NPD6014	Approved
0.5909	Remote Similarity	NPD6012	Approved
0.5909	Remote Similarity	NPD6013	Approved
0.5905	Remote Similarity	NPD6404	Discontinued
0.5897	Remote Similarity	NPD8033	Approved
0.5895	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD1696	Phase 3
0.5872	Remote Similarity	NPD5701	Approved
0.5862	Remote Similarity	NPD7516	Approved
0.5859	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD6672	Approved
0.5859	Remote Similarity	NPD5737	Approved
0.5856	Remote Similarity	NPD6883	Approved
0.5856	Remote Similarity	NPD7102	Approved
0.5856	Remote Similarity	NPD7290	Approved
0.5851	Remote Similarity	NPD6930	Phase 2
0.5851	Remote Similarity	NPD7514	Phase 3
0.5851	Remote Similarity	NPD6931	Approved
0.5842	Remote Similarity	NPD6411	Approved
0.5833	Remote Similarity	NPD7507	Approved
0.5825	Remote Similarity	NPD5210	Approved
0.5825	Remote Similarity	NPD4629	Approved
0.5824	Remote Similarity	NPD8039	Approved
0.5818	Remote Similarity	NPD6011	Approved
0.5816	Remote Similarity	NPD4623	Approved
0.5816	Remote Similarity	NPD4519	Discontinued
0.5812	Remote Similarity	NPD8294	Approved
0.5812	Remote Similarity	NPD8377	Approved
0.5804	Remote Similarity	NPD6869	Approved
0.5804	Remote Similarity	NPD6649	Approved
0.5804	Remote Similarity	NPD6617	Approved
0.5804	Remote Similarity	NPD6847	Approved
0.5804	Remote Similarity	NPD6650	Approved
0.5804	Remote Similarity	NPD8130	Phase 1
0.5794	Remote Similarity	NPD7632	Discontinued
0.5794	Remote Similarity	NPD5211	Phase 2
0.5773	Remote Similarity	NPD3133	Approved
0.5773	Remote Similarity	NPD3666	Approved
0.5773	Remote Similarity	NPD3665	Phase 1
0.5766	Remote Similarity	NPD6373	Approved
0.5766	Remote Similarity	NPD6372	Approved
0.5763	Remote Similarity	NPD8380	Approved
0.5763	Remote Similarity	NPD8296	Approved
0.5763	Remote Similarity	NPD8379	Approved
0.5763	Remote Similarity	NPD8378	Approved
0.5763	Remote Similarity	NPD8335	Approved
0.5758	Remote Similarity	NPD7524	Approved
0.5758	Remote Similarity	NPD7750	Discontinued
0.5752	Remote Similarity	NPD8297	Approved
0.5752	Remote Similarity	NPD6882	Approved
0.5745	Remote Similarity	NPD6929	Approved
0.5743	Remote Similarity	NPD4096	Approved
0.5714	Remote Similarity	NPD4785	Approved
0.5714	Remote Similarity	NPD4191	Approved
0.5714	Remote Similarity	NPD4193	Approved
0.5714	Remote Similarity	NPD4194	Approved
0.5714	Remote Similarity	NPD6926	Approved
0.5714	Remote Similarity	NPD4192	Approved
0.5714	Remote Similarity	NPD368	Approved
0.5714	Remote Similarity	NPD4784	Approved
0.5714	Remote Similarity	NPD6924	Approved
0.5699	Remote Similarity	NPD6925	Approved
0.5699	Remote Similarity	NPD5776	Phase 2
0.5698	Remote Similarity	NPD7341	Phase 2
0.5688	Remote Similarity	NPD5141	Approved
0.5684	Remote Similarity	NPD7332	Phase 2
0.5684	Remote Similarity	NPD4695	Discontinued
0.5678	Remote Similarity	NPD6319	Approved
0.5673	Remote Similarity	NPD5654	Approved
0.5667	Remote Similarity	NPD4243	Approved
0.5657	Remote Similarity	NPD5279	Phase 3
0.5638	Remote Similarity	NPD7145	Approved
0.5638	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD6008	Approved
0.5631	Remote Similarity	NPD4202	Approved
0.563	Remote Similarity	NPD7503	Approved
0.5625	Remote Similarity	NPD857	Phase 3
0.5625	Remote Similarity	NPD6902	Approved
0.562	Remote Similarity	NPD7492	Approved
0.5612	Remote Similarity	NPD4786	Approved
0.5607	Remote Similarity	NPD5286	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data